Antioxidant or age retarder



Pawnee Jan. 11 3,1931

ALBEBT CLIFFORfifQZEfLAKRONQ 0m ASSIGIIOBTQiTHE GOODYEAR TIRE @zlRUBBEiR V COMPANY, on AKRON, OHIO, A CORPOBATIONOFOHIOF No D 'gwingr i ANTIOXIDAN'I OR AGE RETnRDEIR I l/ly iiiizention; reIej teslto-the t feztt nentfof particular relation to at method of preserving, rubbe from the deter o 'et ng efieetsiof ag:

of its objects the, provision of a material;

rubber o1 rubberlilge'inieterials"and it has which, when incofpotated in .1"ubber,-serves to inhibit oxldat on and decay of the rubber.

Another object of the invention, consists in the provision ofa'n antioxidant" or nge -retarder that is jeoln posed of a'substituted" aro-* instio hydioz'iy compound,

' I f Ithts been obse'i ved heretofofe that Certain aroin' a t-1c 'hydroxycompounds,- for example t oz-naphthol or hydroquinone, when incorpo- The crystalline lnate ialinmy'be dissolved and,

* .tural formula lnavyhe This materiel; "1n l'oxvingmethjod.

'thol in f This s mm is t} ten 1 need j u 'u .eqolingjbath "i u'nd' is treated with a; 1n oleuu' lei" ,(juantitpw oil chlorine; ;Thechlorinated material is th'en v treated with an exeesstofvasaturatedstannio ehloride"solutioitzund' dt-ehlor ,B-Haphthol fi i'st] 'r ated into-a rubbeeoompound, act as preservatlves'or age retarders for that material.

1n stei'i :11 which ,fa11's ithin the s c ope of the invention is u-fchlor stutter;

resented 2 "follows D nlv xms wh bout eight parts ofgla precipitates as en oil which soon crystallizes.

V, l'eorystal'lized from-heroinwhiter" The puri fied material has a Ineltingpoint of 7 0 Ci- 1 is preoipitated. from thesolutionlupon wenn u i ing after:the adchtionoffoommonsaltr The V theoretically"possible.

Zinc oxide Sulphur Steario :aoid; Hexaniethyle e= tet Samples of unateriallprepared in accorclance jxt ith the pleeding formula; infwhich oc-ChlQf- B-nap hthol' and F lac-amino ,8-naphthol were employed as, antioxidants, were isub riodsoftime am temperature corresponding r r 'to'foi'tyipoundsof steam pressure. Certain? my b pig fl h w f- 1 ofthe-samples were then immediate 1y su-b-.

e v a t t v V t eity end tens le strength.thet eof. Other "samples Were plaeed in an oxygenbonlbend thePW re'fiet d mme h t fum tion fi 1ed 1December;10, 192? s rig n l 39,261.

-einino ,B-nephthol, which is obtained by reducing oo-IlitlOSO Brnaphthoiwith' sodium hy dirosulphide-in an aqueous alcoholic solution, The reaeti'on "product (we nino fi na-phthol) yield is approximately J 7 5 percenttof that.

.i-fThe' nmte ials dis oussed mayof oourse be ineolrpomted into lvarious rubber compounds with satisfactory results. The following forrn'ule may be employed to obtain an: eXeel- Tent quality of proctuot when any ofthe amines previouslyi.discussed are incorporated ii 1 therein as a-nt'ioxldants or age-reslsters;

e beds? jeeted to c'u 'res Conducted for difieitentipe jeotedto tests inord'erto aseerta-inthe elesi subjeoted fto an air pressure of 5Qpoiinds pet squzu'e nol'l tata temperature of-5'0 4Gi fore PGTTOdOffi days. The letter samp es- Y of Oxygen takihg P 3 6 auringthe test. The i samples wel e also sub ected to tests similar to I those conduotedwith reference to the samples.

cial aging. The following tables contain the results obtained from these tests:

Z-ohlor 2-naphth0l ORIGINAL I Time of wt.

cure Klzs/cm Percent ggg Egg increase wins. at tensile elongadong; e1 ongaf after 6 40$? strength tion tion non tlizggsat AFTER AGING I a-a'mino B-naphthol T ORIGINAL aonn 5 It will be observed from the tables that both antioxidants to alargeextent inhibit the absorption of oxygen by the rubber compoundsinto which they are incorporated and that the samples are of satisfactory tensile strength and'ela'sticity even after having been subjected to the actionofoxygen at a-relar V tively high temperature for a period of six days. Samples of rubber prepared in accordance with the precedingformula, but in which no antioxidant is used, are reduced to resinous masses by such treatment.

Although I have described in detail only thepreferred embodiments of my invention, it will be apparent to'those skilled in the art that it is not so limited, but that various minor modifications may be inside therein without departing from the spirit of the in- V venti'oi claims. \Vllat I claim is:

or from the scope of the appended having the following structural formulaz' in which R is an aminegrou V 2. A meter predate that Ya been turmcomprises vulcanizing it in the ILA method of preserving rubber ivliiclr comprises incorporatingtherein a material ized in the presence of a material having the following structural formula:

in which R is an amine group, said niateria being substantially non-accelerator.

y 4. A rubber product that has'bee-n vulcanized in the presence of AL-aminoB-naphthol. 5..A method of preserving rubber-which comprises vulcaniiing it in the presence of a materialhaving the following structural formula in which R is either a basic nitrogen containing or av chlorine group. I p

6. A method of preserving rubber which comprises vulcanizing it in the presence of a material .havingthe following structural formula: I V

' I R V f q in which'R is either an amino group or a chlorine atom.. r I v 7. A. method of preserving rubberwhich presence of alpha-amino beta-na'phthol.

8 1A method of preserving rubber whichcompmses vulcanizmgit 111 the presence of an alpha-amino beta-naphthol, said material being substantially a non-accelerator of the rate of vulcanization of rubber.

beta-naphthol, said material being snbstan tia'lly anon-accelerator "of the rate of nlgcomprises subjecting it to vulcanization in the presence of' alpha-ohlor beta-naphtholi In Witness whereof, I'havehereuntosigned my name. v 7

Si netlat Akron, in the county of Summit, and tate ofOhio, this 9th1day of December ALBERT M. CLIFFORD.

9. A rubberproduot that has been vul-f .canized'inthepresence of an alphammmo 

